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US4502994A
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Enantiomeric synthesis of 3-amino-4-carbamoyloxymethyl-2-azetidonone-1-sulfate
Assignee: Hoffmann La Roche Inc
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Filing: 1982-12-09
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Granted: 1985-03-05
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Expires: 2002-12-09
Abstract
Abstract A novel enantiomeric synthesis from ascorbic acid of (3S,4S)-3-amino-4-carbamoyloxymethyl-2-azetidinone-1-sulfate, an intermediate for an antibiotic compound.
Inventors
- 👤 Chung-Chen Wei
- 👤 Manfred Weigele
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 20:39
CPC Classifications
C; C07; C07D; C07D417/00; C07D407/00; C07D407/02; C07D407/04; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/085; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/30; C07D417/02; C07D417/12; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
42 words
The compound of the formula ##STR14## wherein R 10 is a conventional amino protecting group; R 9 is hydrogen or taken together with its attached oxygen forms a sulfonyl leaving group; R 11 is hydrogen, lower alkyl, aryl, or halo lower alkyl.
Claim 2
Dependent Claim
42 words
The compound of the formula ##STR14## wherein R 10 is a conventional amino protecting group; R 9 is hydrogen or taken together with its attached oxygen forms a sulfonyl leaving group; R 11 is hydrogen, lower alkyl, aryl, or halo lower alkyl.
Claim 3
Dependent Claim
10 words
The compound of claim 1 wherein R 9 is hydrogen.
Claim 4
Dependent Claim
22 words
The compound of claim 2 wherein R 10 is lower alkoxy carbonyl, aryloxy carbonyl, halo substituted lower alkoxy carbonyl or arylalkoxy carbonyl.
Claim 5
Dependent Claim
10 words
The compound of claim 3 wherein said compound is (2S,3S)-2-benzyloxycarboxamido-3-hydroxy-4-chloroacetoxy-butanamide.
Claim 6
Dependent Claim
13 words
The compound of claim 1 wherein R 9 forms a sulfonyl leaving group.
Claim 7
Dependent Claim
34 words
The compound of claim 5 wherein R 9 is lower alkyl sulfonyl, halosubstituted lower alkylsulfonyl, phenylsulfonyl, halophenylsulfonyl, lower alkylsubstituted phenylsulfonyl, phenyl lower alkylsulfonyl, halosubstituted phenyl lower alkylsulfonyl, or lower alkyl substituted phenyl lower sulfonyl.
Claim 8
Dependent Claim
10 words
The compound of claim 6 wherein said compound is (2S,3S)-2-benzyloxycarbonylamino-3-methanesulfonyloxy-4-chloroacetoxybutanamide.
References Cited (Backward Citations)
US4216008A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-03-04 | 1988-09-03 | 1989-03-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-03-04 | 1992-09-03 | 1993-03-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-03-04 | 1996-09-03 | 1997-03-05 | $7700.00 | Window Closed / Lapsed |